A staple run in the valley, the vineyard climb from Triasso to Triangia is a tough section of uneven steps that seems never-ending. It does end, but you might wish it hadn't because it's just so beautiful. Obviously afterwards the first thing you should do is go and find some Sassella red wine, preferably that made by the cooperative wine sellers in the village of Triasso or by Alfio Mozzi, Valtellina's fastest wine producer.
You can make so many variations of this run, including starting from almost anywhere: Sondrio for a longer climb or Castione for a shorter loop. This one starts and finishes in Postalesio to give your legs a warm-up and warm-down. The trail across the top of the vineyards from Castione is part of the Terrazzamenti trail, and it's just magical.
Above Triangia you've got the option to include the lake or not. I probably would but there's some beautiful pine forest trails that loop around it.
The descent back to Castione goes by the name 'Rodelbahn', as it weaves its way playfully through the woods. Enjoy it.
Year-round route. The wine harvest is in October usually, so that's a great time to see the hustle and bustle along the route.